6-<<<4-chloro-3-(trifluoromethyl)phenyl>-amino>methyl>-2,4-quinazolinediamine acetate | 52128-20-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 6-<<<4-chloro-3-(trifluoromethyl)phenyl>-amino>methyl>-2,4-quinazolinediamine acetate
• 英文别名: 6-({[4-chloro-3-(trifluoromethyl)phenyl]-amino}methyl)-2,4-quinazolinediamine acetate
• CAS: 52128-20-8
• 化学式: C₂H₄O₂*C₁₆H₁₃ClF₃N₅
• 分子量: 427.813
• InChiKey: WKWQQQJBHMIKGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  29.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  127.15
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6-<<<4-chloro-3-(trifluoromethyl)phenyl>-amino>methyl>-2,4-quinazolinediamine acetate 在 sodium nitrite 作用下， 以 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以70%的产率得到6-<<<4-chloro-3-(trifluoromethyl)phenyl>nitrosoamino>methyl>-2,4-quinazolinediamine
  参考文献：
  名称：

  Folate antagonists. 20. Synthesis and antitumor and antimalarial properties of trimetrexate and related 6-[(phenylamino)methyl]-2,4-quinazolinediamines

  摘要：

  A series of 6-[(arylamino)methyl]-2,4-quinazolinediamines have been prepared by catalytic hydrogenation of the requisite 2,4-diamino-6-quinazolinecarbonitriles in the presence of the appropriate benzenamine. Formylation, acetylation, and nitrosation provided N omega derivatives of these compounds. A variety of the compounds exhibited potent antimalarial, antibacterial, and antitumor activity. In particular, 5-methyl-6-[[(3,4,5-trimethoxyphenyl)-amino]methyl]-2, 4-quinazolinediamine (trimetrexate, 15) has shown a broad spectrum of antitumor effects and is undergoing preclinical toxicology evaluation prior to trial in man.

  DOI：

  10.1021/jm00366a018
• 作为产物：
  描述：

  溶剂黄146 、 2-氯-5-氨基三氟甲苯 、 2,4-diamino-6-quinazoline-6-carbonitrile 在 镍 氢气 作用下， 28.0 ℃ 、344.73 kPa 条件下， 反应 22.0h， 以41%的产率得到6-<<<4-chloro-3-(trifluoromethyl)phenyl>-amino>methyl>-2,4-quinazolinediamine acetate
  参考文献：
  名称：

  Folate antagonists. 20. Synthesis and antitumor and antimalarial properties of trimetrexate and related 6-[(phenylamino)methyl]-2,4-quinazolinediamines

  摘要：

  A series of 6-[(arylamino)methyl]-2,4-quinazolinediamines have been prepared by catalytic hydrogenation of the requisite 2,4-diamino-6-quinazolinecarbonitriles in the presence of the appropriate benzenamine. Formylation, acetylation, and nitrosation provided N omega derivatives of these compounds. A variety of the compounds exhibited potent antimalarial, antibacterial, and antitumor activity. In particular, 5-methyl-6-[[(3,4,5-trimethoxyphenyl)-amino]methyl]-2, 4-quinazolinediamine (trimetrexate, 15) has shown a broad spectrum of antitumor effects and is undergoing preclinical toxicology evaluation prior to trial in man.

  DOI：

  10.1021/jm00366a018